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Side view of California Casual outfit with Oliveo leather shorts, Shein patched shirt, neckerchief, Jord bamboo wood watch, Longchamp bag (all own), bomber jacket c/o Shein, and Musse & Cloud wood sandals c/o Coolway

This post addresses how to wear shorts over 40 (and at any age) the modern way in all seasons and even in a buisness casual work place. Read the easy-to-follow tips and get inspired by the shorts outfit ideas.


  1. When Can You Wear Your Shorts?
  2. Should You Stop Wearing Shorts over 50?
  3. Can You Wear Shorts in Alaska in Summer?
  4. How to Style Shorts in Winter?
  5. How to Dress Shorts the California Casual Way?
  6. Ageless Style Linkup


Updated: 4/1/2022

Disclosure: This post has affiliate links.


When Can You Wear Your Shorts?

Most babyboomers and Gen X associate shorts as best for the summer heat, sunshine, fun, play, weekend, and vacation. Well, we only wore them for these events and occasions when we were teenagers and twenty somethings. Most of us stopped wearing them when we moved into a city. After coming to Alaska, I stopped considering shorts a summer item because of fear the many mosquitoes would take my legs as an invitation for lunch, or dinner.


fashion blogger showing how to wear shorts over 40 in leather shorts with button-down shirt
Front view. Oliveo leather shorts, Shein patched button-down shirt, statement belt, neckerchief, Longchamp bag, Jord bamboo wood watch, bomber jacket c/o Shein, and Musse & Cloud wood sandals c/o Coolway


Today, shorts are not only for leisure. They are even work-appropriate in casual environments in form of a short suit. When the short suits came up in the late zero years, I have taken them as an opportunity to wear suits. Scientists in physics-based fields rarely dress up for conferences.


Should You Stop Wearing Shorts over 50?

No. Style doesn’t know age. It’s just a matter of how to wear shorts over 40. Go for a sophisticated way like in the easy-to-copy outfit inspirations in this post.

We can wear what we can style. Click To Tweet

Why is it that there are so many articles in prominent newsletters and magazines that say “Don’t wear shorts after age of 30, 40, ….” (you add the number here). Isn’t it true that shorts look awful and frumpy at any age when they are not styled? And isn’t that true for all clothes?

Style your shorts at any age. #agelessstyle Click To Tweet


Can You Wear Shorts in Alaska in Summer?

Yes. And you better do wear them. In Alaska, many young European work as waiter or waitresses over the summer. They quickly learn that the locals dress much lighter than the tourists. As a result wearing shorts for the summer heat avoids to have to answer the question “Where do you come from?” Alaskan tourists wear long pants and long sleeve shirts or jackets. No, it’s not their fear of mosquitoes, their fear of cold weather.


How to Style Shorts in Winter?

Opaque tights are key to not look like trying too hard, and to stay in thermal comfort. Actually, in winter you can get away with shorter versions than in summer because of the leg coverages by tights. Go for a dark color to give the illusion of slim legs. More on styling leather shorts.


street style chic winter leather shorts outfit inspiration
Irish cable knit sweater, Oliveo custom-made leather shorts, GNW tights Double H lace-up booties, Festina watch, and Alaska lamp trade beads and silver carving necklace


influencer showing how to wear leather shorts with an oversize cable-knit sweater in winter
Oliveo button  down plaid shirt, Oliveo Bermunda leather shorts, GNW tights, Double H lace-up booties, Kieselstein Colrd belt and buckle. You can find another styling idea with this cable knit sweater at the link.


How to Dress Shorts the California Casual Way?

The featured photo shows a California Casual Style inspired shorts outfit idea. When styling leather shorts go with a trendy top like this button down patched shirt. To finish the look add a statement belt, long dangling earrings, wood plateau sandals, a big cuff, and a wood watch. Take a jacket with you when thunderstorms are in the forecast. Add a pop of color and repeat the color at least twice for style (see featured photo).


Ageless Style Linkup

Welcome to the Ageless Style Linkup party. Let’s see your ageless style outfits wearing pastels.

Ageless Style Linkup 1 Theme 10 Women


Please follow us on at least one of our platforms each. Thank you.

Ana ~ Mrs. American Made blog

Daenel ~ Living outside the stacks blog

Debbie ~ Fashion Fairy Dust

Diane ~ Fashion on the 4th floor blog

Jennie ~ A Pocketful of Polka Dots

Jill ~ Doused in Pink blog

Paula ~ Dimples on my What blog

Shelly ~ The Queen in Between blog

Yvonne ~ Funky Forty blog

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Photos of me: G. Kramm

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